“What's the biggest challenge you're facing right now?”
From Chris Voss · Former FBI lead hostage negotiator; author of Never Split the Difference; founder of The Black Swan Group
Why it works
Voss's calibrated questions are open-ended 'what' and 'how' questions that, in his words, work by giving your counterpart 'the illusion of control': they can't be answered yes/no, they implicitly ask for help, and they make the other side do the talking. The Black Swan Group lists 'What is the biggest challenge you face?' as a standard calibrated question precisely because it's almost universally applicable and yields, as Voss puts it, a treasure trove of information. The mechanism is that you learn the buyer's real priority — the one they'd actually spend to fix — instead of confirming the problem you walked in assuming. It also disarms: a question can't be argued with the way an assertion can, so it lowers defences while raising disclosure.
When to ask
At the very start of a discovery or sales conversation, before you've framed anything. It's the question that lets the other person tell you where the pain actually is — reach for it whenever you're tempted to lead with your own diagnosis.
Good follow-ups
- What makes that the biggest one, versus the others?
- How has that been affecting things day to day?
- What's gotten in the way of fixing it so far?
Watch out for
Treating the first answer as the whole truth. The opener gets them talking; the value comes from what you do next — mirror the last few words, label the emotion ('sounds like this has been frustrating'), and let silence pull more out. Founders also misfire by immediately pitching against the named challenge ('great, that's exactly what we solve!'), which snaps the buyer back into a guarded sales frame. Stay curious one beat longer than feels comfortable — the second and third things they say are usually truer than the first.
Where to ask
- Sales callgreat
Voss's go-to calibrated opener — on a sales or discovery call it hands the other side the floor, lowers their guard, and surfaces the pain they actually care about instead of the one your script assumes.
- User interviewgreat
A clean, low-pressure interview opener; because it's open and non-leading, it lets the person set the agenda and tells you which problem is top-of-mind before you bias them with yours.
- In-product surveypoor
The phrasing survives async, but its real power is the live, illusion-of-control dynamic and your ability to follow the thread; in a survey it degrades into a generic open-ended box people skip.
Reworded for this context: “What's the biggest challenge you're facing with this right now?”
- Long-form surveypoor
Calibrated questions are built for a back-and-forth where you mirror and label the answer; a one-shot survey strips the conversational mechanism that makes this work.
Stage: Consider · A question popularized by Chris Voss
Source: https://www.blackswanltd.com/newsletter/using-calibrated-questions%EF%B8%8F-to-win-more-deals